Most games have some sort of paddling-pool-and-water-wings beginning to ease you in: Oolite takes the rather more Darwinian approach of heaving you straight into the ocean, often with a brick or two in your pockets for luck. ~ Disembodied

And finally I discovered why it is no longer working. In the iTunes library, I clearly see that "playlist" has a 'Shuffle" property, so I thought it was a bug that I could not set is any longer.

I just discovered at the bottom of the library that there also exists a "User Playlist" and that has no "Shuffle" property. Also in iTunes, I can not link the shuffle status to a playlist. I only can set it globally in the program. So, now I am convinced that this is no bug in iTunes, but that Apple removed the shuffle option from the playlists and that it is not likely it will return in iTunes.

I'll remove those two lines from Oolite to make iTunes work again. Setting the shuffle and repeat must than be set in iTunes itself. No big deal.

It is better leaving the settings out than forcing the settings by manipulating the iTunes menu, as this requires that the player gives Oolite special privileges to manipulate other programs. It is a potential security risk and not everyone will appreciate such a privileges from a downloaded program they not fully know.